US20160333190A1 - Powder composition of polyarylene ether ketone ketones allowing an excellent castability/coalescence balance suitable for laser sintering - Google Patents

Powder composition of polyarylene ether ketone ketones allowing an excellent castability/coalescence balance suitable for laser sintering Download PDF

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US20160333190A1
US20160333190A1 US15/105,977 US201415105977A US2016333190A1 US 20160333190 A1 US20160333190 A1 US 20160333190A1 US 201415105977 A US201415105977 A US 201415105977A US 2016333190 A1 US2016333190 A1 US 2016333190A1
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composition
powder
polyarylene ether
coalescence
ether ketone
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Benoit Brule
Hervé STER
Cyrille Mathieu
Nadine Decraemer
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Arkema France SA
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Arkema France SA
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints
    • C09D5/033—Powdery paints characterised by the additives
    • C09D5/037—Rheology improving agents, e.g. flow control agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10—Processes of additive manufacturing
    • B29C64/141—Processes of additive manufacturing using only solid materials
    • B29C64/153—Processes of additive manufacturing using only solid materials using layers of powder being selectively joined, e.g. by selective laser sintering or melting
    • B29C67/0077—
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y10/00—Processes of additive manufacturing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • B33Y70/10—Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y80/00—Products made by additive manufacturing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/38—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D7/1216—
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2071/00—Use of polyethers, e.g. PEEK, i.e. polyether-etherketone or PEK, i.e. polyetherketone or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/25—Solid
    • B29K2105/251—Particles, powder or granules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
    • C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium

Definitions

  • the present invention relates to a composition
  • a composition comprising from 99.6% to 99.99% by weight of at least one powder of at least one polyarylene ether ketone and 0.01% to 0.4% by weight of a hydrophilic flow agent.
  • This hydrophilic flow agent is characterized by a gain in mass (amount of water absorbed), after 5 days of conditioning at a relative humidity of 95%, of greater than 0.5%.
  • This gain in mass of the flow agent is determined by Karl Fischer measurement after desorption of the water via a 15-minute treatment at 170° C.
  • This composition is suitable for laser sintering. It in particular allows an excellent castability/coalescence compromise for the powder.
  • Polyarylene ether ketones and more particularly polyether ketone ketones (PEKK) are highly efficient materials. They are used for applications with temperature constraints and/or mechanical or even chemical constraints. These polymers are found in fields as varied as aeronautics, offshore drilling and medical implants. They may be used by molding, extrusion, compression, spinning or laser sintering, especially. However, their use in the latter process requires powder preparation conditions that ensure good flowability allowing implementation in the laser sintering process as described below.
  • the technology of powder sintering under a laser beam serves to manufacture objects in three dimensions such as prototypes and models, but also functional parts, especially in the motor vehicle, nautical, aeronautic, aerospace, medical (prostheses, auditive systems, cell tissues, etc.), textile, clothing, fashion and decorative fields, casings for electronics, telephony, home automation, information technology and lighting.
  • a thin layer of powder is deposited on a horizontal plate maintained in a chamber heated to a certain temperature.
  • the laser supplies the energy required to sinter the powder particles at various points in the layer of powder in a geometry corresponding to the object, for example with the aid of a computer having the shape of the object in its memory and rendering this shape in the form of slices.
  • the horizontal plate is lowered by a value corresponding to the thickness of a layer of powder (for example between 0.05 and 2 mm and generally about 0.1 mm) and a new layer of powder is then deposited.
  • the laser supplies the energy required to sinter the powder particles in a geometry corresponding to this new slice of the object, and so on. The procedure is repeated until the entire object has been manufactured.
  • Powders are thus sought which have, firstly, good flowability and, secondly, good coalescence during the sintering process.
  • US 2004/0 204 531 describes the advantage in polyamide of hydrophobic silicas versus hydrophilic silicas. Specifically, the flowability is deteriorated after moisture uptake in the case of using hydrophilic silicas, whereas it is unchanged in the case of using hydrophobic silicas.
  • PAEK polyarylene ether ketones
  • U.S. Pat. No. 7,847,057 relates to a process for the heat treatment of polyarylene ether ketone powders, which consists in exposing the powder to a heat treatment for over 30 minutes at a temperature 20° C. above the glass transition temperature of the polymer.
  • WO 2012/047 613 also describes a heat treatment applied more particularly to polyether ketone ketone (PEKK) powders, which consists in exposing the powder to a heat treatment for several hours between the transition temperatures of the various crystalline phases, more particularly by approaching the melting point of the polymer, corresponding to the crystalline form having transition at the highest temperature.
  • PEKK polyether ketone ketone
  • the flowability of the powder is thereby improved and the crystallinity resulting from this treatment is conserved during the sintering process, giving the sintered object certain advantageous physical properties, but appearing insufficient for certain applications.
  • the coalescence aspect is not discussed in said patent, and in particular no example demonstrates that the coalescence is effective, modified or even improved by the heat treatment.
  • the invention relates to a composition
  • a composition comprising from 99.6% to 99.99% by weight of at least one powder of at least one polyarylene ether ketone and 0.01% to 0.4% by weight of a hydrophilic flow agent, preferably from 0.01% to 0.2% by weight of a hydrophilic flow agent and, more particularly, preferably from 0.01% to 0.1% by weight of a hydrophilic flow agent.
  • This hydrophilic flow agent is characterized by a gain in mass (amount of water absorbed), after 5 days of conditioning at a relative humidity of 95%, of greater than 0.5%, preferably greater than 0.8%. This gain in mass of the flow agent is determined by Karl Fischer measurement after desorption of the water by a 15-minute treatment at 170° C.
  • the invention also relates to the use of the compositions of the invention and also to the objects manufactured with the aid of these compositions, in particular with the aid of a laser sintering process.
  • PAEK polyarylene ether ketones
  • Ar and Ar 1 each denote a divalent aromatic radical; a minor proportion ( ⁇ 10%) of these units may be replaced with radicals with a valency of greater than 2 to introduce branches.
  • Ar and Ar 1 may preferably be chosen from 1,3-phenylene, 1,4-phenylene, 4,4′-biphenylene, 1,4-naphthylene, 1,5-naphthylene and 2,6-naphthylene;
  • X denotes an electron-withdrawing group; it may preferably be chosen from the carbonyl group and the sulfonyl group, Y denotes a group chosen from an oxygen atom, a sulfur atom, an alkylene group, such as —CH 2 — and isopropylidene.
  • At least 50%, preferably at least 70% and more particularly at least 80% of the groups X are a carbonyl group, and at least 50%, preferably at least 70% and more particularly at least 80% of the groups Y represent an oxygen atom.
  • 100% of the groups X denote a carbonyl group and 100% of the groups Y represent an oxygen atom.
  • PAEK polyarylene ether ketone
  • sequences may be totally para (Formula II), but it would not constitute a departure from the context of the invention to introduce, partially or totally, meta sequences:
  • the polyarylene ether ketone that may be used according to the invention may be semicrystalline or amorphous.
  • the polyarylene ether ketones are polyether ketone ketones comprising a mixture of units IIIA and IIIB such that the mass percentage of terephthalic units relative to the sum of the terephthalic and isophthalic units is between 55% and 85% and preferably between 55% and 70%, ideally 60%.
  • terephthalic unit” and “isophthalic unit” mean the formula of terephthalic acid and isophthalic acid, respectively.
  • polyarylene ether ketones are in the form of powders that may be prepared by grinding or precipitation.
  • the mixtures of various polyarylene ether ketone powders comprise a polyether ketone ketone combined with another polyarylene ether ketone or a mixture of two PEKKs of different chemical structure.
  • a polyarylene ether ketone will be combined with a PEK, PEEKEK, PEEK, PEKEKK or PEKK.
  • the PEKK will be combined with PEK, PEEKEK, PEEK or PEKEKK or a PEKK of different chemical formula, the PEKK representing more than 50% by mass, limit inclusive.
  • hydrophilic flow agents used in the context of the invention may be inorganic pigments preferably chosen from silicas and aluminas.
  • hydrophilic silicas used in the context of the invention are constituted of silicon oxide. They are fumed silicas without any specific treatment, unlike the hydrophobic silicas, which are fumed silicas that have undergone a chemical treatment such as grafting with dimethylchlorosilane. It would not constitute a departure from the context of the invention to use silicas synthesized via another manufacturing method.
  • the silicas commonly used are commercial products whose trade name is Aerosil® (supplied by Evonik) or Cab-O-Sil® (supplied by Cabot).
  • silicas are composed of nanometric primary particles (typically between 5 and 50 nm for fumed silicas). These primary particles are combined to form aggregates. In use as flow agent, silicas are found in various forms (elementary particles and aggregates).
  • the powders or powder mixtures comprising hydrophilic flow agents used in the context of the invention may, where appropriate, be supplemented or contain various compounds.
  • reinforcing fillers especially mineral fillers such as carbon black, nanotubes, which may or may not be carbon-based, fibers (glass, carbon, etc. fibers), which may or may not be ground, stabilizers (light stabilizers, in particular UV stabilizers, and heat stabilizers), optical brighteners, colorants, pigments, energy-absorbing additives (including UV absorbers) or a combination of these fillers or additives.
  • the coalescence will be judged to be proportionately better the more invisible the steel plate has become following the coalescence/film formation of the powder.
  • Kepstan® 6003 PL powder from the company Arkema containing 60% of terephthalic units relative to the sum of the terephthalic and isophthalic units, whose particle size has a Dv50 of 50 ⁇ m plus or minus 5 ⁇ m, was supplemented with 0.4% of Cab-O-Sil® TS-610 silica in a Magimix kitchen blender at high speed for 100 seconds.
  • the Dv50 is also known as the volume median diameter, which corresponds to the particle size value which divides the population of particles examined exactly into two.
  • the Dv50 is measured according to standard ISO 9276—parts 1 to 6. In the present description, a Malvern Mastersizer 2000 particle size analyzer is used, and the measurement is taken in the liquid route by laser diffraction on the powder.
  • the silica Cab-O-Sil® TS-610 is a fumed silica that has been made hydrophobic by treatment with dimethylchlorosilane. It will be referred to hereinbelow as “TS-610”.
  • the powder has excellent flowability (time ⁇ 10 s, 0 taps for a 17 mm funnel), but the coalescence, estimated as described above, is very poor, the steel plate still being clearly visible.
  • the silica may thus be an anti-coalescer at a high content.
  • Kepstan® 6003 PL powder from the company Arkema containing 60% of terephthalic units relative to the sum of the terephthalic and isophthalic units, whose particle size has a Dv50 of 50 ⁇ m plus or minus 5 ⁇ m, was supplemented with Cab-O-Sil® TS-610 silica in a Magimix kitchen blender at high speed for 100 seconds.
  • a second sample of the same Kepstan powder is supplemented with Cab-O-Sil® M-5 silica according to the same protocol.
  • the silica Cab-O-Sil® M-5 is a hydrophilic fumed silica that has not undergone any specific treatment. It will be referred to hereinbelow as “M-5”.
  • silica improve the flowability and they are thus both potential flow agents for PEKK.
  • Kepstan® 6003 PL powder from the company Arkema is supplemented in the Magimix blender either with 0.05% Cab-O-Sil® TS-610 silica or with 0.05% Cab-O-Sil® M-5 silica.
  • These powders are, on the one hand, stored at 23° C. and 50% relative humidity up to moisture saturation (in the case, for example, of storage of the powder before machine use).
  • the moisture content is measured by the Karl Fischer method (desorption of water from the Kepstan® powder by treatment for 20 minutes at 250° C.). On the other hand, the powders are dried overnight at 140° C. The moisture content is also measured by the Karl Fischer method (same protocol as above).
  • the moisture contents of 0.5% and 0.53% correspond to the state of the material saturated with moisture at 23° C. and 50% relative humidity.
  • the moisture contents of 0.25% correspond to the state of the material after drying at 140° C. overnight.
  • the moisture contents are not affected by the nature of the silica.
  • Example 2 Three samples of Example 2 (not supplemented, supplemented with 0.2% of hydrophobic silica (TS-610), supplemented with 0.2% of hydrophilic silica (M-5)) are deposited on three steel plates.
  • TS-610 hydrophobic silica
  • M-5 hydrophilic silica
  • coated plates are placed in an oven maintained at 340° C. for 15 minutes.
  • FIGS. 2 and 3 visually and under binoculars (Stemi SV11 from Zeiss).
  • the binocular images confirm the preceding observations: there are areas where locally the steel plate can still be seen in the case of the non-supplemented powder and of the powder supplemented with 0.2% of TS-610 silica, whereas, in the case of the powder supplemented with M-5 silica, the steel plate is no longer visible. This confirms the better coalescence of the powder supplemented with M-5 during the oven treatment.

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US15/105,977 2013-12-20 2014-12-17 Powder composition of polyarylene ether ketone ketones allowing an excellent castability/coalescence balance suitable for laser sintering Abandoned US20160333190A1 (en)

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FR13.63201 2013-12-20
FR1363201A FR3015506B1 (fr) 2013-12-20 2013-12-20 Composition de poudres de poly-arylene-ether-cetone-cetones autorisant un excellent compromis coulabilite et coalescence adaptees au frittage laser
PCT/FR2014/053386 WO2015092272A1 (fr) 2013-12-20 2014-12-17 Composition de poudres de poly-arylene-ether-cetone-cetones autorisant un excellent compromis coulabilite et coalescence adaptees au frittage laser

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10322542B2 (en) * 2014-12-16 2019-06-18 Arkema France Method for producing an object by melting a polymer powder in a powder sintering device
EP3659785A1 (fr) * 2018-11-29 2020-06-03 Ricoh Company, Ltd. Poudre pour former un objet tridimensionnel, dispositif de formation, procédé de formation et poudre
US11186717B2 (en) * 2015-12-21 2021-11-30 Shpp Global Technologies B.V. Enhanced powder flow and melt flow of polymers for additive manufacturing applications
US11534824B2 (en) 2018-03-15 2022-12-27 Hewlett-Packard Development Company, L.P. Composition
US11998977B2 (en) 2018-03-15 2024-06-04 Hewlett-Packard Development Company, L.P. Build material composition with metal powder and freeze-dried heteropolymer

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019055737A1 (fr) * 2017-09-15 2019-03-21 Arkema Inc. Procédés et produits de fabrication additive par extrusion de polyethercétonecétones
WO2019122226A1 (fr) * 2017-12-20 2019-06-27 Solvay Specialty Polymers Usa, Llc Procédé de production d'un copolymère peek-pemek et copolymère obtainu au moyen du procédé
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US11407906B2 (en) 2022-08-09
EP3083793B1 (fr) 2021-04-07
RU2016129183A (ru) 2018-01-25
US20190040269A1 (en) 2019-02-07
JP2017508019A (ja) 2017-03-23
FR3015506B1 (fr) 2017-04-21
CN106103564A (zh) 2016-11-09
WO2015092272A1 (fr) 2015-06-25
FR3015506A1 (fr) 2015-06-26
EP3083793A1 (fr) 2016-10-26

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